[(1R)-2-[(benzoyloxy)methyl]-3-oxocyclobutyl]methyl benzoate

• ChemBase ID: 162172
• Molecular Formular: C20H18O5
• Molecular Mass: 338.35392
• Monoisotopic Mass: 338.11542368
• SMILES: C1([C@@H](CC1=O)COC(=O)c1ccccc1)COC(=O)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1)OC[C@@H]1CC(=O)C1COC(=O)c1ccccc1
• InChI: InChI=1S/C20H18O5/c21-18-11-16(12-24-19(22)14-7-3-1-4-8-14)17(18)13-25-20(23)15-9-5-2-6-10-15/h1-10,16-17H,11-13H2/t16-,17?/m0/s1
• InChIKey: RYWNYUWMBMTYBG-BHWOMJMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R)-2-[(benzoyloxy)methyl]-3-oxocyclobutyl]methyl benzoate
• IUPAC Traditional name: [(1R)-2-[(benzoyloxy)methyl]-3-oxocyclobutyl]methyl benzoate
• Synonyms: (2S-trans)-2,3-Bis[(benzoyloxy)methyl]cyclobutanone; (2S,3S)-2,3-Bis(benzoyloxymethyl)cyclobutanone

Database IDs

• CAS Number: 132294-16-7
• PubChem SID: 162256307
• PubChem CID: 71314029

CALCULATED PROPERTIES

• Acid pKa: 17.216625
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.780166
• LogD (pH = 7.4): 3.780166
• Log P: 3.780166
• Molar Refractivity: 91.4389 cm^3
• Polarizability: 35.482403 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate

DETAILS

Toronto Research Chemicals - B410710

Intermediate in the preparation of carbocyclic nucleoside derivatives.

REFERENCES

• Lee-Ruff, E., et al.: J. Med. Chem., 39, 5276 (1996)